International Journal of Molecular Sciences

Article Plant Natural Sources of the Endocannabinoid (E)-β-Caryophyllene: A Systematic Quantitative Analysis of Published Literature

Massimo E. Maffei † Department of Life Sciences and Systems Biology, University of Turin, Via Quarello 15/a, 10135 Turin, Italy; massimo.maff[email protected]; Tel.: +39-011-670-5967 This work is dedicated to Husnu Can Baser for his 70th birthday. †


Received: 7 August 2020; Accepted: 4 September 2020; Published: 7 September 2020


Abstract: (E)-β-caryophyllene (BCP) is a natural sesquiterpene hydrocarbon present in hundreds of plant species. BCP possesses several important pharmacological activities, ranging from pain treatment to neurological and metabolic disorders. These are mainly due to its ability to interact with the cannabinoid receptor 2 (CB2) and the complete lack of interaction with the brain CB1. A systematic analysis of plant species with essential oils containing a BCP percentage > 10% provided almost 300 entries with species belonging to 51 families. The essential oils were found to be extracted from 13 plant parts and samples originated from 56 countries worldwide. Statistical analyses included the evaluation of variability in BCP% and yield% as well as the statistical linkage between families, plant parts and countries of origin by cluster analysis. Identified species were also grouped according to their presence in the Belfrit list. The survey evidences the importance of essential oil yield evaluation in support of the chemical analysis. The results provide a comprehensive picture of the species with the highest BCP and yield percentages.

Keywords: plant species; essential oil; yield; percentages of (E)-β-caryophyllene; Belfrit list; plant part; geographical origin

1. Introduction The endogenous cannabinoid system (ECS) plays an important role in the immune response to an infection. At present, two cannabinoid (CB) receptors are described: cannabinoid type 1 receptor (CB1) and cannabinoid type 2 receptor (CB2), both G-protein coupled receptors [1]. The CB2 receptor represents the peripheral CB, due to its expression on circulating immune cells. However, studies have also found CB2 expression in the brain, such as cerebellum and microglial cells [2]. The CB2 receptor is involved in the attenuation of inflammatory immune responses. CB2 receptor pathway activation entails the suppression of cytokine release from immune cells and thereby dampening of the inflammatory response (immunosuppression) [3]. (E)-β-caryophyllene (BCP) is a bicyclic sesquiterpene hydrocarbon which is present in the essential oil of several plant species [4]. The Research Institute for Fragrance Materials (RIFM) evaluated BCP safety and the molecule has been approved by the Food and Drug Administration and by the European Food Safety Authority as a flavoring agent, which can be used in cosmetic and food additives [5]. Reports on oral sub-chronic toxicity support the safety of BCP for its proposed use also in medical food products [5]. BCP has been reported to be active against several disorders, with particular reference to cancer, chronic pain and inflammation [2]. Non-clinical BCP toxicity and an absence of adverse effects have been described [6]. Moreover, BCP can act as a selective agonist of CB2 [1], it activates peroxisome proliferator-activated receptor-α (PPAR α)[7] and has been recently involved in the prevention of

Int. J. Mol. Sci. 2020, 21, 6540; doi:10.3390/ijms21186540 www.mdpi.com/journal/ijms Int. J. Mol. Sci. 2020, 21, 6540 2 of 37 lipid accumulation and in the improvement of glucose uptake [8]. Therefore, BCP is a plant-derived bioactive molecule able to improve health and prevent lifestyle diseases. Moreover, the specificity of BCP for the CB2 receptor, mainly expressed in peripheral tissues, and its inability to bind CB1, which is predominantly expressed at the level of the central nervous system, implies that its action is devoid of the known psychoactive effects associated with the activation of CB1 [1,2,9,10]. In this context, BCP is an interesting alternative to the use of Cannabis. Owing to the growing importance of BCP, it was interesting to evaluate the occurrence of this important endocannabinoid in plant species used for the extraction of essential oils. Therefore, the aim of this work was to look for plant natural sources of BCP in order to provide the pharmaceutical, nutraceutical and aroma industries a summary of plant species, parts used for extraction and geographical origin of plants producing BCP. Moreover, additional information was provided with regards to the content and yield of BCP as well as the occurrence of selected species in the Belfrit list [11], which includes botanicals allowed in food supplements and ensures compliance of botanicals in terms of quality and safety.

2. Results and Discussion The database search (performed in July 2020) for the term caryophyllene provided 5867 entries. The search was then refined by selecting all papers with a chemical composition description. This selection provided 2604 entries, which were individually analyzed in order to select papers providing information on BCP percentage > 10%. Papers were then analyzed and the species binomial name, the plant family, the country of origin of samples and the plant part extracted were reported along with the BCP percentage and yield percentage. The total number of selected species was 295 (Table1). Table1 also lists the presence of the species in the Belfrit list [11]. In general, the 295 species belonged to 51 families and were reported from 56 countries worldwide. The essential oil containing BCP was extracted from 13 different plant parts. Out of 295 species, 34 were found to be listed in the Belfrit list, whereas for 51 species no data were available on the yield percentage. In many cases, the researchers used a small amount of plant parts (ranging from a few g to 200–300 g) from which it was impossible to evaluate the oil yield. However, in the majority of the other cases the yield was provided and hence reported (Table1). Int. J. Mol. Sci. 2020, 21, 6540 3 of 37

Table1. Occurrence of (E)-β-caryophyllene (BCP) in different plant species. n.a., data not available, the essential oil (E.O.) yield is expressed as volume/weight percentage.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Anacardiaceae Rhus coriaria L. Iran YES fruits 0.55 34.3 249 [12] Anacardiaceae Spondias pinnata (Linn. F.) Kurz Egypt NO leaves 2.00 49.9 268 [13] Annonaceae Annona muricata L. Bénin YES leaves 0.10 13.6 30 [14] Annonaceae Annona densicoma Mart. Brazil NO leaves 0.10 14.4 31 [15] Annonaceae Annona senegalensis Pers. Burkina Faso NO leaves 0.73 19.1 32 [16] Annonaceae Annona squamosa L. India YES leaves 0.12 22.9 33 [17] Annonaceae Artabotrys hexapetalus (L. f.) Bhandare Vietnam NO flowers 0.94 11.4 38 [18] odorata (Lam.) Hook.f. and Annonaceae Cananga Australia YES leaves 0.30 52.0 62 [19] Thomson glauca Pierre ex Engler and Annonaceae Cleistopholis Ivory Coast NO leaves 0.19 26.2 81 [20] Diels Annonaceae Fissistigma rubiginosum Merr. Vietnam NO leaves 0.30 28.1 125 [21] Annonaceae Goniothalamus multiovulatus Ast Vietnam NO stems 0.21 35.7 135 [22] sp. (Dunal) Hook.f. and Annonaceae Melodorum Australia NO leaf 0.15 26.7 182 [23] Thomson horsfieldii (Bennett) Baillon ex Annonaceae Miliusa Australia NO leaves 0.1 20.2 188 [24] Pierre Annonaceae Mitrephora zippeliana Miq. Australia NO leaves 0.30 18.1 189 [19] Annonaceae Polyalthia oliveri Engl. Ivory Coast NO leaves 0.13 31.4 237 [25] Annonaceae Pseuduvaria hylandii Jessup Australia NO leaves 0.50 24.1 242 [26] Annonaceae Uvariodendron calophyllum R. E. Fries Cameroon NO stem barks 0.52 32.5 284 [27] erecta (Hudson) Coville subsp. Apiaceae Berula Serbia NO aerial parts 0.01 14.9 52 [28] erecta Apiaceae Bilacunaria anatolica A. Duran Turkey NO aerial parts 0.14 10.3 54 [29] Apiaceae Centella asiatica L. South Africa YES aerial parts 0.06 19.1 75 [30] Apiaceae Conium maculatum L. Iran NO aerial parts 0.20 15.3 85 [31] Apiaceae Dorema aucheri Boiss. Iran NO leaves 0.40 35.7 108 [32] Apiaceae Eryngium vesiculosum Labill. Australia NO aerial parts n.a. 20.3 116 [33] Apiaceae Ferula glauca L. Iran NO leaves 0.07 24.9 123 [34] Int. J. Mol. Sci. 2020, 21, 6540 4 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Apiaceae Grammosciadium pterocarpum Boiss. Turkey NO aerial parts n.a. 15.3 136 [35] microcarpum (M. Bieb.) B. Apiaceae Hippomarathrum Iran NO aerial parts 0.85 15.75 145 [36] Fedtsch Apiaceae Hippomarathrum boissieri Reuter et Hausskn Turkey NO aerial parts 0.40 25.6 146 [37] Apiaceae Laser trilobum (L.) Borkh. Iran NO aerial parts 1.80 22.4 165 [38] Apiaceae Oenanthe divaricata (R. Br.) Mabb. Spain NO aerial parts 0.20 15.3 206 [39] viridiflorum (Turcz.) Apiaceae Ostericum China NO aerial parts 0.03 24.3 210 [40] Kitagawa Apiaceae Pimpinella kotschyana Boiss. Iran NO seeds 5.16 49.9 224 [41] Apiaceae Prangos uloptera DC. Iran NO aerial parts 0.70 18.2 240 [42] Apiaceae Zosima absinthifolia Link Iran NO aerial parts 0.20 22.2 295 [43] Apocynaceae Allamanda cathartica L. Brazil NO flowers n.a. 15.7 21 [44] Apocynaceae Aspidosperma cylindrocarpon Muell. Arg. Brazil NO leaves 0.03 14.3 45 [45] Apocynaceae Tabernaemontana catharinensis A. DC. Brazil NO leaves 0.30 56.9 272 [46] Araliaceae Schefflera stellata (Gaertn.) Harms India NO leaves 0.10 19.2 260 [47] Aristolochiaceae Aristolochia elegans Mast. Argentina NO leaves n.a. 27.8 36 [48] Aristolochiaceae Aristolochia fordiana Hemsl China NO aerial parts 0.19 11.1 37 [49] Asteraceae Achillea asplenifolia Vent. Serbia NO aerial parts 0.10 17.6 4 [50] leaf and Asteraceae Achyrocline alata (D.C.) Brazil NO 4.00 16.0 5 [51] flowers Asteraceae Acroptilon repens (L.) Iran NO aerial parts 0.11 10.0 6 [52] fastigiatum (Gardn.) R. M. Asteraceae Ageratum Brazil NO branches 0.20 34.9 13 [53] King et H. Rob Asteraceae Ageratum conyzoides L. Portugal NO flowers 0.17 24.6 14 [54] Asteraceae Anthemis altissima L. Iran NO flowers 0.03 25.3 34 [55] Asteraceae Artemisia verlotiorum Lamotte France YES aerial parts 0.20 12.7 39 [56] Asteraceae Artemisia parviflora Roxb India NO aerial parts 0.20 15.3 40 [57] roxburghiana Besser var. Asteraceae Artemisia India NO aerial parts 0.85 18.4 41 [58] purpurascens (Jacq.) Hook Asteraceae Artemisia capillaris Thunb South Korea YES aerial parts n.a. 11.1 42 [59] Asteraceae Artemisia. stricta Edgew. f. stricta Pamp India NO aerial parts 0.46 13.4 43 [60] Asteraceae Artemisia. lavandulaefolia DC South Korea NO aerial parts n.a. 16.1 44 [61] Asteraceae Aspilia africana (Pers.) C. D. Adams Nigeria NO leaves 0.02 10.8 46 [62] Int. J. Mol. Sci. 2020, 21, 6540 5 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Asteraceae Baccharis. articulata (Lam.) Pers Argentina NO aerial parts n.a. 16.8 48 [63] Asteraceae Bidens pilosa L. Cameroon NO leaves n.a. 27.1 53 [64] zlatiborensis Zlatkovic, Asteraceae Centaurea Serbia NO flowers n.a. 28.3 73 [65] Novakovic and Janackovic Asteraceae Centaurea appendicigera C. Koch Turkey NO aerial parts 0.18 17.5 74 [66] Asteraceae Centratherum punctatum Cass Nigeria NO leaves n.a. 16.6 76 [67] Asteraceae Chromolaena odorata L. Togo NO aerial parts 0.50 25.2 78 [68] Asteraceae Conyza bonariensis (L.) Cronquist Brazil NO aerial parts 0.20 14.4 87 [69] Asteraceae Cyanthillium cinereum (L.) H. Rob Ivory Coast NO roots n.a. 17.0 100 [70] Asteraceae Dendranthema indicum (L.) Des Moul. China NO aerial parts 0.08 13.8 106 [71] Asteraceae Emilia sonchifolia (L.) DC. India NO aerial parts n.a. 22.7 110 [72] Asteraceae Epaltes alata Steetz Niger NO leaves 0.30 24.0 111 [73] Asteraceae Eremanthus erythropappus (DC.) MacLeish Brazil NO leaves 0.12 29.3 113 [74] Asteraceae Erigeron ramosus (Walt.) B.S.P. Korea NO flowers 0.40 24.0 114 [75] Asteraceae Eriocephalus luederitzianus O.Hoffm. South Africa NO aerial parts 0.10 13.3 115 [76] Asteraceae Eupatorium triplinerve Vahl India NO leaves 0.40 14.7 120 [77] Asteraceae Flourensia campestris Argentina NO aerial parts 0.02 15.3 127 [78] Asteraceae Helichrysum indutum Humbert Madagascar NO aerial parts 0.19 33.1 141 [79] Asteraceae Helichrysum kraussii Sch. Bip. South Africa NO aerial parts n.a. 30.7 142 [80] Asteraceae Helichrysum melaleucum Rchb. ex Holl. Spain NO aerial parts 0.10 35.4 143 [39] Asteraceae Koanophyllon villosum (Sw.) King et Robins Cuba NO aerial parts 0.45 17.0 160 [81] Asteraceae Laggera oloptera (DC.) C. D. Adams Cameroon NO leaves 0.05 20.4 161 [82] pyrrhapappa var. pyrrhopappa Asteraceae Microglossa Kenya NO leaves 0.40 20.3 185 [83] (A. Rich) Agnew cordata (Burm.f.) B.L. Asteraceae Mikania Ivory Coast NO leaves 0.63 11.8 187 [84] Robinson var. cordata Asteraceae Oyedaea verbesinoides DC. Venezuela NO leaves 0.05 27.1 211 [85] grande Hemsl. var. nelsonii Asteraceae Perymenium Costa Rica NO leaves 0.30 30.5 217 [86] (Robins. and Greenm.) Fay japonicus (Siebold and Zucc.) Asteraceae Petasites Japan NO leaves 0.02 21.9 218 [87] Maxim. Asteraceae Pluchea carolinensis (Jacq.) Sweet Martinique NO leaves 0.11 21.1 236 [88] Int. J. Mol. Sci. 2020, 21, 6540 6 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Asteraceae Porophyllum obscurum (Spreng.) D.C. Argentina NO leaves 0.30 14.1 238 [89] Asteraceae Solidago decurrens Lour China NO leaves 0.37 15.4 266 [90] Asteraceae Tagetes patula L. Austria NO flowers 0.15 53.5 273 [91] Asteraceae Tagetes erecta L. Iran YES flowers 0.35 35.2 274 [92] Asteraceae Tanacetum punctatum (Desr.) Grierson Iran NO aerial parts 0.1 21.1 275 [93] trilobus var. galpinii (Hutch. Asteraceae Tarchonanthus South Africa NO leaves 0.14 30.4 276 [94] and E.Phillips) Paiva Asteraceae Vernonia chalybaea Mart. Brazil NO aerial parts 0.10 39.1 287 [95] Asteraceae Vernonia scorpioides (Lam.) Pers. Brazil NO aerial parts 0.10 30.6 288 [96] Asteraceae Xanthium strumarium L. Pakistan NO leaves n.a. 17.5 291 [97] Asteraceae, Leptocarpha rivularis DC. Chile NO aerial parts 0.15 21.1 168 [98] Atherospermataceae Daphnandra repandula (F.Muell.) F.Muell. Australia NO aerial parts 0.20 12.2 105 [99] Boraginaceae Cordia leucocephala Moric Brazil NO leaves 0.04 39.0 91 [100] Boraginaceae Cordia multispicata Cham. Brazil NO leaves 0.25 56.6 92 [101] Burseraceae Bursera aromatica (Proctor) Jamaica NO leaves 0.03 21.7 59 [102] Burseraceae Bursera microphylla A. Gray USA NO oleo-gum-resin 2.10 72.9 60 [103] Burseraceae Canarium parvum Leen. Vietnam NO leaves 0.20 18.7 63 [104] Burseraceae Dacryodes edulis (G. Don) H. J. Lam Nigeria NO leaves 0.08 26.0 103 [105] Burseraceae Protium heptaphyllum (Aubl.) March. Brazil YES leaves 0.30 18.6 241 [106] Cannabaceae Cannabis sativa L. ssp. spontanea Austria YES aerial parts n.a. 16.2 64 [107] Cannabaceae Cannabis sativa L. Italy YES flowers 0.10 23.8 65 [108] Cannabaceae Humulus lupulus L. USA YES aerial parts n.a. 22.0 148 [109] Caryophyllaceae Dianthus caryophyllus L. Iran YES aerial parts n.a. 34.8 107 [110] harringtonia K.Koch subsp. Cephalotaxaceae Cephalotaxus India NO twigs 0.01 21.1 77 [111] harringtonia Clusiaceae Clusia nemorosa G. Mey Brazil NO fruits 0.30 48.6 83 [112] Clusiaceae Garcinia atroviridis Griff. ex T. Anders. Malaysia NO fruits n.a. 23.8 128 [113] Clusiaceae Kielmeyera rugosa Choisy Brazil NO fruits n.a. 16.4 158 [114] Clusiaceae Pentadesma butyracea Sabine Benin NO barks 0.08 74.0 214 [115] Clusiaceae Psorospermum corymbiferum Hochr Nigeria NO leaves 0.02 46.8 245 [116] Convolvulaceae Convolvulus persicus L. Iran NO aerial parts 0.04 47.0 86 [117] Int. J. Mol. Sci. 2020, 21, 6540 7 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Cupressaceae Cedrus atlantica G. Manetti Algeria NO twigs 0.02 11.4 72 [118] macrocarpa Sibth. and Sm. Cupressaceae Juniperus Turkey NO fruits n.a. 29.6 156 [119] (Jom) Cupressaceae Thuja orientalis L. Egypt NO aerial parts 2.60 24.0 281 [120] rhizomes Cyperaceae Cyperus glomeratus L. Serbia NO 0.06 12.6 102 [121] and roots Ehretiaceae Varronia curassavica Jacq. Brazil NO leaves 0.6 41.2 285 [122] Ehretiaceae Varronia schomburgkii (DC.) Borhidi French Guiana NO aerial parts 0.06 47.0 286 [123] Euphorbiaceae Acalypha fruticosa Forssk India NO leaves 1.40 42.0 2 [124] Euphorbiaceae Alchornea tiliifolia (Benth.) Muell. Vietnam NO aerial parts n.a. 10.7 20 [125] rhamnifolioides Pax and Euphorbiaceae Croton Brazil NO leaf 0.21 33.3 94 [126] Hoffm Euphorbiaceae Croton glandulosus L. Brazil NO aerial parts 0.12 53.2 95 [127] Euphorbiaceae Croton pulegiodorus Baill. Brazil NO aerial parts 5.00 20.9 96 [128] muellerianus (O. Kuntze) Euphorbiaceae Phyllanthus Nigeria NO leaves 0.12 41.9 223 [129] Exell Fabaceae Bauhinia rufa Steud. Brazil NO leaves 0.01 15.8 50 [130] Fabaceae Bowdichia virgilioides Kunt Brazil YES seeds 2.20 44.1 57 [131] Fabaceae Caesalpinia decapetala (Roth) Alston Japan NO aerial parts 0.07 17.2 61 [132] Fabaceae Copaifera langsdorffii Desf. Brazil YES oleoresins 28.00 72.0 88 [133] Fabaceae Copaifera multijuga Hayne Brazil NO oleoresins n.a. 57.5 89 [134] Fabaceae Copaifera reticulata Ducke Brazil NO oleoresins n.a. 68.0 90 [135] Fabaceae Dalea carthagenensis L. Colombia NO leaves 0.15 20.7 104 [136] Fabaceae Eperua duckeana Cowan Brazil NO leaves n.a. 31.8 112 [137] Fabaceae Glycyrrhiza triphylla Fisch. and C.A.Mey Iran NO aerial parts 0.50 25.4 134 [138] Fabaceae Psoralea bituminosa L Italy NO leaves 0.10 23.2 244 [139] Fabaceae Rynchosia minima DC. Kenya NO aerial parts 0.10 30.4 252 [140] Flacourtiaceae Casearia decandra Jacq. Brazil NO leaves 0.20 13.0 67 [141] Flacourtiaceae Casearia sylvestris Swart. Brazil NO leaves 0.60 27.5 68 [142] Geraniaceae Geranium wallichianum D. Don ex Sweet India NO aerial parts n.a. 15.9 130 [143] Gramineae Elyonurns muticus (Sprengel) O.Kuntze Brazil NO leaves 0.45 17.9 109 [144] Int. J. Mol. Sci. 2020, 21, 6540 8 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Gramineae Melinis minutiflora P. Beauv Kenya NO aerial parts 0.01 24.2 180 [145] nymphaeifolia (C.Presl) Hernandiaceae Hernandia Australia NO leaves 0.01 43.8 144 [146] Kubitzki Hypericaceae Hypericum brasiliense Choisy Brazil NO aerial parts 0.10 29.5 150 [147] Hypericaceae Hypericum perforatum L. Iran YES aerial parts n.a. 25.05 151 [148] baccifera subsp. dealbata Hypericaceae Vismia Venezuela NO leaves 0.07 45.7 289 [149] (Kunth) Ewan Juglandaceae Juglans regia L. India YES leaves 0.02 15.5 155 [150] Lamiaceae Aegiphila lhotzkiana Cham. Brazil NO leaves 0.02 27.5 9 [151] Lamiaceae Ajuga parviflora Benth. India NO aerial parts n.a. 22.4 18 [152] Lamiaceae Ajuga comata Stapf. Iran NO aerial parts n.a. 30.9 19 [153] Lamiaceae Ballota nigra L. Algeria YES aerial parts n.a. 24.6 49 [154] Lamiaceae Clerodendrum polycephalum Baker Nigeria NO leaves 0.16 28.9 82 [155] Lamiaceae Colquhounia coccinea Wall. India NO flower 0.20 53.2 84 [156] Lamiaceae Cunila incana Benth. Brazil NO aerial parts 0.72 11.3 98 [157] Lamiaceae Cyclotrichium. strussii Bornm Iran NO aerial parts 0.37 16.9 101 [158] Lamiaceae Glechoma hederacea L. Lithuania NO aerial parts 0.05 14.2 131 [159] Lamiaceae Glechon marifolia Benth. Brazil NO leaves 1.40 32.2 132 [160] Lamiaceae Hoslundia opposita Vahl. Ivory Coast NO leaves 0.04 24.8 147 [161] Lamiaceae Hymenocrater calycinus (Boiss.) Benth. Iran NO aerial parts 0.20 32.8 149 [162] canum (Pohl ex Benth.) Lamiaceae Hyptidendron Brazil NO leaves 0.82 41.6 152 [163] Harley Lamiaceae Hyptis mutabilis (Rich.) Briq. Argentina NO aerial parts n.a. 59.4 153 [164] Lamiaceae Hyptis suaveolens (L.) Poit. Bénin YES fruits 0.10 43.7 154 [165] iberica (M. Bieb.) Fisch and Lamiaceae Lallenmantia Turkey NO aerial parts n.a. 18.3 162 [166] CA Mey ocymifolia (Burm.f.) Lamiaceae Leonotis South Africa NO leaves 0.06 30.8 166 [167] M.Iwarsson Lamiaceae Leonurus sibiricus L. Argentina NO aerial parts n.a. 35.2 167 [164] Lamiaceae Leucas aspera (Willd.) Link India NO aerial parts 0.30 34.2 169 [168] Lamiaceae Leucas indica (L.) R.Br India NO aerial parts n.a. 51.1 170 [169] bourgaei subsp. caricum Lamiaceae Marrubium Tunisia NO aerial parts 0.07 23.2 175 [170] P.H.Davis Lamiaceae Marsypianthes chamnedrys (Vahl) Kuntze Brazil NO aerial parts n.a. 15.1 176 [171] Int. J. Mol. Sci. 2020, 21, 6540 9 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Lamiaceae Melissa romana Miller Italy NO aerial parts 0.30 15.8 181 [172] Lamiaceae Mentha longifolia (L.) Hudson Iran NO aerial parts 0.41 23.2 183 [173] Lamiaceae Micromeria myrtifolia Boiss. and Hohen. Turkey NO aerial parts 0.20 40.8 186 [174] Lamiaceae Mosla soochowensis Matsuda China NO aerial parts 0.05 12.8 191 [175] Lamiaceae Nepeta fissa C.A. Mey Iran NO aerial parts 0.25 33.1 200 [176] Lamiaceae Nepeta curviflora Boiss. Lebanon NO aerial parts 0.30 50.2 201 [177] Lamiaceae Ocimum tenuiflorum L. India YES aerial parts 0.33 30.0 203 [178] Lamiaceae Origanum majorana L. Algeria YES aerial parts 1.20 26.0 207 [179] Lamiaceae Orthodon dianfhera Maxim. Vietnam NO aerial parts 0.20 52.9 208 [180] Lamiaceae Orthosiphon pallidus Royle, ex Benth India NO aerial parts n.a. 17.4 209 [181] frutescens var. japonica Lamiaceae Perilla China YES leaves 0.11 37.2 215 [182] (Hassk.) H.Hara crinita Cav. ssp. mauritanica Lamiaceae Phlomis Tunisia NO aerial parts 0.10 40.8 220 [183] Munby Lamiaceae Phlomis rigida Labill. Turkey NO aerial parts 0.05 38.7 221 [184] Lamiaceae Platostoma menthoides (L.) A. J. Paton Sri Lanka NO aerial parts 0.50 37.0 233 [185] Lamiaceae Plectranthus rugosus Wall. India NO leaves n.a. 38.4 234 [186] Lamiaceae Pycnostachys eminii Gürke Ethiopia NO leaves 0.13 21.6 246 [187] Lamiaceae Rosmarinus officinalis L Lebanon YES aerial parts 0.09 12.9 251 [188] Lamiaceae Salvia palaefolia Kunth Colombia NO aerial parts 0.06 32.2 253 [189] Lamiaceae Salvia bracteata Banks and Soland Iran NO aerial parts 0.28 41.4 254 [190] Lamiaceae Salvia hydrangea DC. ex Benth. Iran NO aerial parts 0.20 33.4 255 [191] Lamiaceae Salvia nemorosa L. Iran NO aerial parts 0.12 41.6 256 [192] Lamiaceae Salvia virgata Jacq. Iran NO aerial parts 0.48 46.6 257 [193] Lamiaceae Salvia canariensis L. Spain NO aerial parts 4.00 30.2 258 [194] Lamiaceae Salvia montbretii Benth. Turkey NO aerial parts 0.10 32.8 259 [195] Lamiaceae Scutellaria havanensis Jacq. Cuba NO leaves 0.18 75.6 261 [196] brevibracteata Stapf. subsp. Lamiaceae Scutellaria Turkey NO aerial parts n.a. 36.4 262 [197] pannosula clandestina subsp. Lamiaceae Sideritis peloponnesiaca (Boiss. and Greece NO aerial parts 1.00 16.4 263 [198] Heldr.) Baden Lamiaceae Sideritis phlomoides Boiss. and Bal. Turkey NO aerial parts 0.20 30.7 264 [199] Lamiaceae Stachys viticina Boiss. Turkey NO aerial parts 0.20 62.3 269 [200] Int. J. Mol. Sci. 2020, 21, 6540 10 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Lamiaceae Teucrium arduini L. Croatia NO aerial parts 0.35 35.4 277 [201] Lamiaceae Teucrium flavum L. Iran NO leaves 0.20 30.7 278 [202] Lamiaceae Teucrium siculum (Raf.) Guss. Italy NO aerial parts 0.10 30.9 279 [203] turredanum Losa and Lamiaceae Teucrium Spain NO aerial parts 0.60 32.0 280 [204] Rivas-Goday Lamiaceae Viticipremna queenslandica Munir Australia NO leaves n.a. 33.6 290 [205] Lamiaceae Ziziphora taurica M.Bieb. subsp. taurica Turkey NO aerial parts 0.80 24.8 294 [206] Lauraceae Aiouea costaricensis (Mez) Kosterm. Costa Rica NO leaf 0.10 12.0 17 [207] Lauraceae Alseodaphne peduncularis Meisn Malaysia NO leaves n.a. 24.0 27 [208] Lauraceae Aniba riparia (Nees) Mez Brazil NO leaves 0.30 16.9 29 [209] Lauraceae Beilschmiedia penangiana Gamble Malaysia NO aerial parts 0.10 12.6 51 [210] Lauraceae Cassytha pubescens R.Br. Australia NO aerial parts 0.10 30.9 69 [211] tamala (Ham) Nees and Lauraceae Cinnamomum Pakistan NO leaves 0.03 25.3 79 [212] Eberm. Lauraceae Litsea helferi Hook.f. Vietnam NO leaves 0.30 14.2 172 [213] Lauraceae Nectandra lanceolata Ness Brazil NO leaves 0.20 32.5 198 [214] foliosa (Nees) Gamble var. Lauraceae Neolitsea India NO leaves 0.10 35.3 199 [215] caesia (Meisner) Gamble Lauraceae Ocotea duckei Vattimo-Gil Brazil NO leaves 0.70 60.5 204 [216] Lauraceae Ocotea splendens (Meisn.) Baill Brazil NO leaves 0.35 51.0 205 [217] Lauraceae Persea americana Mill. Nigeria YES leaves 0.20 43.9 216 [218] Lauraceae Phoebe porphyria (Griseb.) Mez. Argentina NO aerial parts 0.15 19.3 222 [219] Magnoliaceae Magnolia obovata Thunb. Japan NO leaves 0.05 23.7 173 [220] Malvaceae Pachira glabra Pasq. Nigeria NO leaves 0.71 14.5 212 [221] Malvaceae Triumfetta rhomboidea Jacq. Burkina-Faso NO aerial parts 0.02 24.2 282 [222] Meliaceae Aglaia odorata Lour. Thailand NO stem 0.07 10.2 15 [223] Meliaceae Aphanamixis polystachya (Wall.) R.Parker Bangladesh NO wood n.a. 19.4 35 [224] Meliaceae Cedrela fissilis Vellozo Brazil NO leaves 0.06 26.3 70 [225] macrophylla Vahl. ssp. Meliaceae Guarea Brazil NO leaves 0.15 10.0 137 [226] tuberculata Vellozo Moraceae Ficus benjamina L. Nigeria NO leaves n.a. 17.0 124 [227] Myricaceae Morella pensylvanica (Mirbel) Kartesz Canada NO aerial parts 0.15 14.5 190 [228] Myristicaceae Gymnacranthera canarica (King) Warb. India NO leaves 0.01 23.4 138 [229] Int. J. Mol. Sci. 2020, 21, 6540 11 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Myristicaceae Knema kunstleri Warb. Malaysia NO aerial parts 0.12 23.2 159 [230] Myristicaceae Myristica malabarica Lam. India NO leaves 0.05 27.3 197 [229] Myrtaceae Blepharocalyx salicifolius O.Berg Brazil NO leaves 0.90 22.9 55 [231] Myrtaceae Eucalyptus leptophleba F. Muell. Australia NO leaves 0.01 11.4 118 [232] Myrtaceae Eugenia stipitata McVaugh ssp. sororia Portugal NO leaves 0.35 22.7 119 [233] Myrtaceae Feijoa sellowiana Berg. France NO fruits 0.10 12.0 121 [234] Myrtaceae Marlierea silvatica Kiaersk Brazil NO leaves 0.30 25.4 174 [235] sphaerodendra var. microphylla Myrtaceae Melaleuca (Virot) Craven and J.W. New Caledonia NO leaves 0.10 28.8 178 [236] Dawson Myrtaceae Myrcia cuprea (O. Berg) Kiaersk. Brazil NO aerial parts 0.10 39.1 194 [237] Myrtaceae Myrcianthes pseudo-mato (Legr.) Mc. Vaugh Argentina NO leaves 0.30 18.9 195 [238] Myrtaceae Myrciaria tenella (DC.) Berg Brazil NO leaves 0.40 25.1 196 [239] Myrtaceae Ochrosperma lineare (C.T. White) Trudgen Australia NO aerial parts 0.30 11.6 202 [240] Myrtaceae Plinia edulis (Vell.) Sobral Brazil NO leaves 0.10 21.2 235 [241] Myrtaceae Psidium striatulum DC. Brazil NO leaves 0.10 28.6 243 [242] Myrtaceae Syzygium aromaticum L. Morocco YES buds 8.58 27.5 270 [243] Myrtaceae Syzygium grande (Wight) Walp. Vietnam NO stem 0.12 29.3 271 [244] Myrtaceae Uromyrtus australis A. J. Scott Australia NO leaves 0.12 20.7 283 [245] Papilionaceae Meristotropis xanthioides Vassilez Iran NO aerial parts 3.20 11.8 184 [246] Phyllanthaceae Actephila excelsa (Dazl.) Muell. Vietnam NO leaves 0.15 11.2 7 [247] Pinaceae Abies nephrolepis (Khingan fir) South Korea NO needles 0.40 10.8 1 [248] Pinaceae Pinus pinaster Aiton Morocco YES needles 0.38 22.2 225 [249] Pinaceae Pinus armandii Franch. Scotland NO needles n.a. 36.3 226 [250] Pinaceae Pinus bungeana Zucc. South Korea NO needles 0.31 27.2 227 [251] Pinaceae Pinus halepensis Mill. Turkey NO needles n.a. 25.9 228 [252] tuberculatum var. tuberculatum Piperaceae Piper Brazil NO leaves n.a. 26.3 229 [253] (Micq.) CDC guineense Schumach. and Piperaceae Piper Cameroon NO seeds 1.1 57.6 230 [254] Thonn. Piperaceae Piper nigrum L. India YES seeds n.a. 45.3 231 [255] Int. J. Mol. Sci. 2020, 21, 6540 12 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. Piperaceae Piper maingayi Hk. F. Malaysia NO seeds 0.21 39.6 232 [256] Piperaceae Pothomorphe peltata (L.) Miq. Brazil NO leaves 0.20 68.0 239 [257] Plantaginaceae Adenosma indianum (Lour.) Merr. China NO aerial parts 0.29 10.32 8 [258] Podocarpaceae Afrocarpus mannii (Hook.f.) C.N.Page S. Tomé e Principe NO leaves 0.15 13.1 12 [259] Ptaeroxylaceae Cedrelopsis grevei H. Baillon Madagascar NO barks n.a. 10.6 71 [260] Rosaceae Agrimonia eupatoria L. Iran YES flowers 1.20 42.8 16 [261] Rosaceae Rosa canina L. Tunisia YES flowers 1.40 32.0 250 [262] Rubiaceae Cruciata laevipes Opiz Italy YES aerial parts 0.70 19.0 97 [263] Rubiaceae Geophila repens (L.) I.M. Johnst China NO aerial parts 0.07 23.3 129 [264] Rutaceae Aegle marmelos (L.) Corr. Nepal YES leaves 0.29 29.6 10 [265] Rutaceae Amyris elimifera L. Cuba NO leaves 0.60 37.8 28 [266] Rutaceae Atalantia buxifolia (Poir.) Oliv. China NO leaves 0.36 25.8 47 [267] Rutaceae Boenninghausenia albiflora Reichb. India NO flowers 0.20 13.1 56 [268] Rutaceae Citrus garrawayi F.M.Bailey Australia NO leaves 0.20 17.6 80 [269] Rutaceae Feroniella lucida (Scheff.) Swing Thailand NO leaves 0.12 26.6 122 [270] Rutaceae Flindersia pimenteliana F.Muell. Australia NO leaves 0.03 16.9 126 [271] Rutaceae Haplophyllum villosum (M. B.) G. Don Iran NO aerial parts 0.22 13.1 139 [272] Rutaceae Medicosma obovata T.G. Hartley Australia NO aerial parts 0.40 17.2 177 [273] Rutaceae Melicope peninsularis T.G. Hartley Australia NO leaves 0.10 49.0 179 [274] Rutaceae Murraya paniculata L. Brazil NO leaves 0.03 57.6 192 [275] Rutaceae Murraya koenigii (L.) Spreng India YES leaves 0.1 45.9 193 [276] Rutaceae Pamburus missionis (Wight) Swingle India NO leaves 0.05 25.4 213 [277] Rutaceae Spiranthera odoratissima A. St. Hil. Brazil NO leaves n.a. 23.8 267 [278] Rutaceae Zanthoxylum veneficum F.M.Bailey Australia NO leaves 0.10 36.3 292 [279] Sapindaceae Acer truncatum Bunge China NO leaves n.a. 12.9 3 [280] Schisandraceae Kadsura coccinea (Lem.) A.C. Smith China NO roots 0.20 24.9 157 [281] Scrophulariaceae Buddleia asiatica Lour. India NO leaves 0.30 15.8 58 [282] Scrophulariaceae Capraria biflora L. Brazil NO leaves 0.09 29.6 66 [283] Solanaceae Solanum stipulaceum Roem and Schult Brazil NO flowers 0.08 25.8 265 [284] Verbenaceae Aloysia virgata Juss. Cuba NO aerial parts n.a. 15.4 22 [285] Verbenaceae Lantana montevidensis Briq Brazil NO leaves 0.13 31.5 163 [286] Verbenaceae Lantana camara L. Madagascar NO aerial parts 0.08 43.61 164 [287] Int. J. Mol. Sci. 2020, 21, 6540 13 of 37

Table 1. Cont.

Family Genus Species and Auth Geogr. Origin of Sample Belfrit List Part Used E.O. Yield% BCP% Code Ref. myriocephala Schltdl. et Verbenaceae Lippia Costa Rica NO leaves 0.08 16.1 171 [288] Cham. Verbenaceae Petitia domingensis Jacq. Cuba NO flowers n.a. 35.7 219 [289] corrorima (Braun) P.C.M. Zingiberaceae Aframomum Ethiopia NO leaves 0.50 60.7 11 [290] Jansen Zingiberaceae Alpinia purpurata (Viell.) Fiji NO flowers 0.05 24.2 23 [291] Zingiberaceae Alpinia conchigera Griff. Malaysia NO rhizomes 0.14 10.0 24 [292] Zingiberaceae Alpinia mutica Roxb. Vietnam NO fruit 0.17 22.6 25 [293] pinnanensis T. L. Wu and Zingiberaceae Alpinia Vietnam NO fruit 0.23 11.4 26 [294] Senjen Zingiberaceae Costus afer Ker–Grawl Nigeria NO leaves n.a. 12.3 93 [295] Zingiberaceae Curcuma longa L. India YES rhizomes 2.20 9.8 99 [296] Zingiberaceae Etlingera elatior (Jack) R. M. Smith Malaysia NO leaves 0.70 10.7 117 [297] Zingiberaceae Globba schomburgkii Hook. f. India NO aerial parts 0.01 31.7 133 [298] Zingiberaceae Hedychium coronarium Koen. Brazil YES leaves 0.68 43.0 140 [299] Zingiberaceae Renealmia breviscapa Poepp. and Endl. Brazil NO rhizomes 0.01 62.3 247 [300] Zingiberaceae Renealmia alpinia (Rottb.) Maas Brazil NO leaves 0.50 22.9 248 [301] Zingiberaceae Zingiber nimmonii Dalzell India NO rhizomes 0.04 42.2 293 [302] Int. J. Mol. Sci. 2020, 21, 6540 14 of 37

The essential oil yield of 243 species ranged from 0.001 to 8.58%, whereas the BCP percentage of all selected species ranged from 9.8 (the threshold minimum level for species selection) to 75.6% (Table2), providing an average percentage of 0.42% for yield and 27.4% for BCP. As shown in Table2, variability was higher for yield percentages than for BCP percentage. The reason for the yield and BCP variability depends on several factors, including plant part, the quantity of plant material distilled and, most of all, the genetic variability and phenotypic plasticity of plants [303–306].

Table 2. General statistics on BCP and yield percentages of plant species listed in Table1.

Specification Essential Oil Yield Percentage of BCP Number of cases 243 295 Range Minimum 0.00 9.8 Maximum 8.58 75.6 Mean 0.42 27.4 S.E.M. 0.06 0.8 S.D. 0.87 13.6 C.V. % 2.09 0.5 S.E.M., standard error of the mean; S.D., standard deviation; C.V., coefficient of variation.

In order to look for plant species with the highest BCP and yield percentages, a scatter plot was obtained, as depicted in Figure1. The highest yield and BCP percentages were found for Copaifera langsdorffii. High BCP percentages but with decreasing yields were found for Bursera microphylla, Scutellaria havanensis and Pentadesma butyracea. Copaifera species, popularly known as copaiba oil, are widely used in Brazilian popular medicine and the genus is known for its high essential oil yield and BCP content [135,307,308]. The genus Bursera belongs to the plant family Burseraceae and contains several aromatic spices producing oleo-gum resins, such as the traditional incenses, frankincense and myrrh [309]. Pentadesma butyracea (Clusiaceae) is a dense forest species which is found in the center and north of Benin forests whose bark, rough and deeply cracked, exudes a thick resinous juice, of reddish yellow color [115]. The Scutellaria genus (Lamiaceae) consists of plants which are widely distributed throughout the world; S. butyracea is an endemic plant native from Havana and is ethnomedically used for several purposes because of its BCP content [196]. High yields with lower BCP percentages were found for Acalypha fruticosa, Achyrocline alata, Agrimonia eupatoria, Bowdichia virgilioides, Bursera microphylla, Croton pulegiodorus, Curcuma longa, Glechon marifolia, Laser trilobum, Meristotropis xanthioides, Origanum majorana, Pimpinella kotschyana, Piper guineense, Rosa canina, Salvia canariensis, Spondias pinnata, Syzygium aromaticum and Thuja orientalis. All other species had a yield ranging from 0.004 to 1% and a BCP content ranging from 9.8 to 55 % (Figure1). The plant part that contained the highest content of BCP was then analyzed. In order to evidence the statistical linkage between the plant parts, a cluster analysis was calculated by considering as category the plant part and as variables the number of species, the BCP% and the yield% reported in Table1 (Figure2). Euclidean distances were calculated by using the average linkage method. Five clusters were evidenced: the first cluster was made by plant parts reported in more than 100 species and was dominated by leaves and aerial parts, which contained in general a BCP percentage lower than 28%. The other four clusters were made by plant parts reported in less than 16 species. These four clusters were further subdivided according to their BCP content (Figure2). As expected, the highest BCP percentage was found in oleo-gum resins (cluster 2), followed by roots, barks and branches (cluster 3). Flowers and buds (cluster 4) showed a high yield, whereas twigs and woods (cluster 5) had both low yields and BCP percentages (Figure2). Int. J. Mol. Sci. 2020, 21, 6540 15 of 37

Figure 1. Scatter plot of BCP percentage vs. yield percentage. The yield axis is represented as a power of 0.3 scale in order to evidence species with yields ranging from 0.004 to 3%. Numbers correspond to plant species listed in Table1. Filled circles outline the species outside the central group of all other species (hollow circles).

Figure 2. Cluster analysis of BCP and yield percentages according to the plant part used for extraction. Euclidean distances are calculated with average linkage method. Five clusters are evident (see text for explanation).

Table3 summarizes the statistical analysis of BCP and yield percentages reported from di fferent plant parts. Int. J. Mol. Sci. 2020, 21, 6540 16 of 37

Table 3. Average percentages of BCP and yields from plant parts as reported in plant species listed in Table1.( S.E.M.); n.c., not computable; E.O., essential oil. ± Number of Plant Part BCP % E.O. Yield % Species Aerial Parts 115 25.19 ( 1.10) 0.42 ( 4.85) ± ± Barks 3 39.03 ( 18.59) 0.30 ( 0.22) ± ± Branches 1 34.90 ( n.c.) 0.20 ( n.c.) ± ± Buds 1 27.50 ( n.c.) 8.58 ( n.c.) ± ± Flowers 16 29.29 ( 3.11) 0.41 ( 0.13) ± ± Fruits 9 26.93 ( 4.43) 0.24 ( 0.07) ± ± Leaves 128 27.58 ( 1.15) 0.30 ( 0.04) ± ± Oleo-gum resin 4 66.13 ( 4.54) 15.50 ( 8.30) ± ± Rhyzomes 5 27.38 ( 10.65) 0.49 ( 0.43) ± ± Roots 7 39.77 ( 5.37) 1.77 ( 0.92) ± ± Stems 3 25.07 ( 7.66) 0.13 ( 0.04) ± ± Twigs 2 16.25 ( 4.85) 0.02 ( 0.01) ± ± Wood 1 19.40 ( n.c.) 0.42 ( n.c.) ± ±

The next analysis was at the familial level. A cluster analysis was calculated with average linkage method by using data of Table1 by considering as a category the plant families and the species number, yield% and BCP% as variables. The results of the cluster analysis show the presence of 6 clusters (Figure3). The first cluster is made by the Asteraceae and the Lamiaceae which consist of a number of species > 50 and a BCP% < 31. The second cluster gathers all families whose species have a BCP% > 35%; in this cluster, the Magnoliaceae and the Papilionaceae are separated in a subcluster because of their high BCP% and low yield%, whereas the Fabaceae (which include the above mentioned C. langsdorffii) are separated in a subcluster because of their high yield %. The third cluster is made by families with a number of species > 13 and a BCP% > 23%; here, the Lauraceae, the Apiaceae and the Zingiberaceae are separated in a subcluster because of their higher BCP%. The genus Ocotea is one of the largest of the Lauraceae family, with approximately 350 species distributed throughout tropical and subtropical America. O. splendens, as many other Ocotea species [212] is characterized by a high percentage of BCP [217]. In the Apiaceae family, the species P. kotschyana spreads widely through Anatoly, Iran (northwest, west and center) and north of Iraq and contains BCP in all plant parts [41]. The family Zingiberaceae is well known for producing essential oils that are used to prevent and control several diseases; the species R. breviscapa was found to possess a high percentage of BCP [300]. The fourth cluster is made by families with a BCP% > 26 and a subcluster separates the Atherospermaceae, the Flacourtiaceae and the Meliaceae because of their BCP%. The fifth cluster is made by families with a BCP% < 25 and the Plantaginaceae are separated in a subcluster because of their relatively higher yield%. Finally, the sixth cluster is made by plant families with a low BCP percentage and a subcluster separates the Hernandiaceae, the Juglandaceae, the Phyllanthace and the Ptaeroxylaceae because of their BCP content lower than 11%. Int. J. Mol. Sci. 2020, 21, 6540 17 of 37

Figure 3. Cluster analysis of BCP and yield percentages according to the plant families. Euclidean distances are calculated with average linkage method. Six clusters are evident (see text for explanation).

Table4 describes the statistical data related to plant families. The next analysis aimed to evidence the geographical areas from which the plant species listed in Table1 were collected. A cluster analysis was calculated with average linkage method, considering the country of origin as a category of their species number, yield% and BCP% as variables. The results of the cluster analysis show the presence of 6 clusters (Figure4). The first cluster gathers countries with the highest number of species and a BCP percentage higher than 28%; here, a subcluster separates Brazil from India and Iran because of the higher number of species, in agreement with the literature data [310]. The second and third clusters identify countries where BCP has the highest percentages, whereas the fourth cluster gathers countries with a number of species higher than 8. The fifth cluster is made by countries where the BCP content is the lowest, whereas the sixth cluster is made by two subclusters with BCP percentages ranging from 18 to 25%. One of these subclusters is made by countries (Colombia, Fiji, Kenya, Morocco, Niger, North Korea, Portugal and Togo) where the species had a BCP percentage higher than 24% (Figure4). Int. J. Mol. Sci. 2020, 21, 6540 18 of 37

Table 4. Average percentages of BCP and yields from plant families belonging to the plant species reported in Table1.( S.E.M.); n.c., not computable; n.a., not available; E.O., essential oil. ± Family Number of Species BCP% E.O. Yield% Anacardiaceae 2 13.25 ( 2.65) n.a. ± Annonaceae 15 22.17 ( 1.26) 0.20 ( 0.05) ± ± Apiaceae 16 30.96 ( 4.15) 0.37 ( 0.14) ± ± Apocynaceae 3 17.63 ( 3.05) 0.26 ( 0.10) ± ± Araliaceae 1 39.00 (n.c.) 0.04 (n.c.) Aristolochiaceae 2 26.65 ( 3.75) 0.21 ( 0.13) ± ± Asteraceae 50 27.94 ( 1.92) 0.47 ( 0.14) ± ± Atherospermaceae 1 32.20 (n.c.) 0.06 (n.c.) Boraginaceae 2 22.95 ( 10.15) 0.15 ( 0.10) ± ± Burseraceae 5 24.20 ( 4.83) 0.14 ( 0.02) ± ± Cannabaceae 3 20.24 ( 5.14) 0.27 ( 0.14) ± ± Caryophyllaceae 1 46.60 (n.c.) 0.48 (n.c.) Cephalotaxaceae 1 41.60 (n.c.) 0.82 (n.c.) Clusiaceae 5 25.85 ( 6.84) 0.29 ( 0.19) ± ± Convolvulaceae 1 15.10 (n.c.) n.a. Cupressaceae 3 23.83 ( 9.60) 1.59 ( 0.84) ± ± Cyperaceae 1 38.40 (n.c.) n.a. Ehretiaceae 2 41.95 ( 15.65) 1.10 (n.c.) ± Euphorbiaceae 6 25.60 ( 15.42) 0.42 ( 0.46) ± ± Fabaceae 11 36.92 ( 6.15) 3.89 ( 3.45) ± ± Flacourtiaceae 2 27.75 ( 3.15) n.a. ± Geraniaceae 1 13.10 (n.c.) 0.22 (n.c.) Gramineae 2 27.90 ( 13.50) 0.19 ( 0.09) ± ± Hernandiaceae 1 9.80 (n.c.) 2.20 (n.c.) Hypericaceae 3 41.10 ( 15.86) 0.13 ( 0.05) ± ± Juglandaceae 1 10.00 (n.c.) 0.15 (n.c.) Lamiaceae 57 31.03 ( 2.03) 0.41 ( 0.17) ± ± Lauraceae 13 29.33 ( 3.14) 0.38 ( 0.18) ± ± Magnoliaceae 1 56.90 (n.c.) 0.30 (n.c.) Malvaceae 2 19.70 ( 5.20) 0.11 ( 0.04) ± ± Meliaceae 4 30.55 ( 9.27) 0.14 ( 0.03) ± ± Moraceae 1 37.80 (n.c.) 0.60 (n.c.) Myricaceae 1 18.10 (n.c.) 0.30 (n.c.) Myristicaceae 3 42.93 ( 10.61) 1.35 ( 0.85) ± ± Myrtaceae 15 23.49 ( 2.17) 0.27 ( 0.08) ± ± Papilionaceae 1 52.00 (n.c.) 0.30 (n.c.) Phyllanthace 1 10.70 (n.c.) n.a. Pinaceae 5 23.22 ( 5.33) 0.20 ( 0.06) ± ± Piperaceae 5 19.70 ( 2.26) 0.23 ( 0.07) ± ± Plantaginaceae 1 20.90 (n.c.) 5.00 (n.c.) Podocarpaceae 1 12.90 (n.c.) n.a. Ptaeroxylaceae 1 11.30 (n.c.) 0.72 (n.c.) Rosaceae 2 18.00 ( 6.60) 0.10 ( 0.08) ± ± Rubiaceae 2 17.15 ( 0.25) 0.03 (n.c.) ± Rutaceae 15 22.97 ( 2.69) 0.27 ( 0.06) ± ± Sapindaceae 1 36.30 (n.c.) n.a. Schisandraceae 1 32.00 (n.c.) 1.40 (n.c.) Scrophulariaceae 2 21.75 ( 0.65) 0.10 (n.c.) ± Solanaceae 1 12.20 (n.c.) 0.20 (n.c.) Verbenaceae 5 24.70 ( 6.58) 1.59 ( 1.20) ± ± Zingiberaceae 13 28.61 ( 4.25) 0.22 ( 0.06) ± ± Int. J. Mol. Sci. 2020, 21, 6540 19 of 37

Figure 4. Cluster analysis of BCP and yield percentages according to the country of origin of extracts. Euclidean distances are calculated with average linkage method. Six clusters are evident (see text for explanation).

Table5 summarizes the statistics related to countries of origin. Int. J. Mol. Sci. 2020, 21, 6540 20 of 37

Table 5. Average percentages of BCP and yields from countries from which plant species reported in Table1 were sampled. ( S.E.M.); n.c., not computable; n.a., not available; E.O., essential oil. ± Country Number of Species BCP% E.O. Yield% Algeria 3 20.67 ( 4.65) 0.61 ( 0.59) ± ± Argentina 8 25.85 ( 5.41) 0.19 ( 0.07) ± ± Australia 18 25.70 ( 2.98) 0.18 ( 0.04) ± ± Austria 2 34.85 ( 18.65) 0.15 (n.c.) ± Bangladesh 1 19.40 (n.c.) n.a. Benin 3 43.77 ( 17.44) 0.09 ( 0.01) ± ± Brazil 56 33.01 ( 2.20) 1.08 ( 0.59) ± ± Burkina Faso 2 21.65 ( 2.55) 0.38 ( 0.36) ± ± Cameroon 4 34.40 ( 8.12) 0.56 ( 0.30) ± ± Canada 1 14.50 (n.c.) 0.15 (n.c.) Chile 1 21.10 (n.c.) 0.15 (n.c.) China 11 19.26 ( 2.54) 0.18 ( 0.04) ± ± Colombia 2 26.45 ( 5.75) 0.11 ( 0.05) ± ± Costa Rica 3 19.53 ( 5.61) 0.16 ( 0.07) ± ± Croatia 1 35.40 (n.c.) 0.35 (n.c.) Cuba 5 36.30 ( 10.85) 0.41 ( 0.12) ± ± Egypt 2 36.95 ( 12.95) 2.30 ( 0.30) ± ± Ethiopia 2 41.15 ( 19.55) 0.32 ( 0.19) ± ± Fiji 1 24.20 (n.c.) 0.05 (n.c.) France 2 12.35 ( 0.35) 0.15 ( 0.05) ± ± French Guian 1 47.00 (n.c.) 0.06 (n.c.) Greece 1 16.40 (n.c.) 1.00 (n.c.) India 29 27.00 ( 2.32) 0.34 ( 0.11) ± ± Iran 30 28.69 ( 2.02) 0.67 ( 0.22) ± ± Italy 5 22.54 ( 2.55) 0.26 ( 0.12) ± ± Ivory Coast 5 22.24 ( 3.48) 0.25 ( 0.13) ± ± Jamaica 1 21.70 (n.c.) 0.03 (n.c.) Japan 3 20.93 ( 1.94) 0.05 ( 0.02) ± ± Kenya 3 24.97 ( 2.94) 0.17 ( 0.12) ± ± Lebanon 2 31.55 ( 18.65) 0.20 ( 0.11) ± ± Lithuania 1 14.20 (n.c.) 0.05 (n.c.) Madagascar 3 29.10 ( 9.74) 0.14 ( 0.06) ± ± Malaysia 7 20.56 ( 3.98) 0.25 ( 0.11) ± ± Martinique 1 21.10 (n.c.) 0.11 (n.c.) Morocco 2 24.85 ( 2.65) 4.48 ( 4.10) ± ± Nepal 1 29.60 (n.c.) 0.29 (n.c.) New Caledonia 1 28.80 (n.c.) 0.10 (n.c.) Niger 1 24.00 (n.c.) 0.30 (n.c.) Nigeria 10 25.87 ( 4.39) 0.19 ( 0.09) ± ± North Korea 1 24.00 (n.c.) 0.40 (n.c.) Pakistan 2 21.40 ( 3.90) 0.03 (n.c.) ± Portugal 2 23.65 ( 0.95) 0.26 ( 0.09) ± ± S. Tomé e Prince 1 13.10 (n.c.) 0.15 (n.c.) Scotland 1 36.30 (n.c.) n.a. Serbia 4 18.35 ( 3.47) 0.05 ( 0.03) ± ± South Africa 5 24.86 ( 3.65) 0.09 ( 0.02) ± ± South Korea 4 16.30 ( 3.83) 0.36 ( 0.05) ± ± Spain 4 28.23 ( 4.44) 1.23 ( 0.93) ± ± Sri Lanka 1 37.00 (n.c.) 0.50 (n.c.) Thailand 2 18.40 ( 8.20) 0.10 ( 0.03) ± ± Togo 1 25.20 (n.c.) 0.50 (n.c.) Tunisia 3 32.00 ( 5.08) 0.52 ( 0.44) ± ± Turkey 14 29.21 ( 3.51) 0.25 ( 0.08) ± ± USA 2 47.45 ( 25.45) 2.10 (n.c.) ± Venezuela 2 36.40 ( 9.30) 0.06 ( 0.01) ± ± Vietnam 11 22.38 ( 4.01) 0.28 ( 0.08) ± ± Int. J. Mol. Sci. 2020, 21, 6540 21 of 37

In order to separate which species containing BCP were also represent in the Belfrit list, a scatter plot was obtained by selecting BCP% and yield% as variables (Figure5). C. langdorffii, S. aromaticum, C. longa and B. virgilioides were characterized by a yield ranging from 2 to 28%, with varying percentages of BCP; on the other hand, high percentages of BCP but lower yields% were found for A. eupatoria, H. coronarium, C. odorata, P. americana and M. keonigi. All other species showed both lower yields and BCP percentage.

Figure 5. Scatter plot of BCP% and yield% of plant species present in the Belfrit list. The yield axis is scaled as a power of 0.2 in order to evidence species with yields ranging from 0.02 to 8.6%. 1, Pinus pinaster Aiton; 2, Ocimum tenuiflorum L.; 3, Aegle marmelos (L.) Corr.; 4, Protium heptaphyllum (Aubl.) March.; 5, Artemisia verlotiorum Lam rinus officinalis L.; 6, Annona squamosa L.; 7, Cannabis sativa L.; 8, Centella asiatica L.; 9, Annona muricata L.; 10, Rosmarinus officinalis L; 11, Perilla frutescens var. japonica (Hassk.) H. Hara. 3. Materials and Methods

3.1. Systematic Analysis of BCP-Containing Plant Species After a preliminary search by using different databases, the work was performed by using Clarivate Analytics Web of Science as a database (http://apps.webofknowledge.com). The basic search criterion was on the general search for the molecule (caryophyllene), then the exclusion criteria were the presence of BCP and a percentage of BCP in the reported results higher than 10%. Papers reporting the occurrence of BCP where then downloaded and saved as a pdf for further reading and collection of information.

3.2. Statistical Analysis The binomial name of the species (including the author), the family of belonging, the plant part used, the country of origin of the sample, the yield and the BCP percentages were inserted in a database by using Systat® 10 software (Systat Software Inc., San Jose, California, U.S.A.). Data were organized in columns and used for further processing. Average values along with ranges, standard deviation (S.D.), standard error of the mean (S.E.M.) and coefficient of variation (C.V.) were calculated by considering as grouping categories either the species, families, country of origin or plant part used. Int. J. Mol. Sci. 2020, 21, 6540 22 of 37

As a classification statistical method, a cluster analysis was calculated by considering for each category the total number of species, the BCP percentage and the yield percentage by using Systat® 10 software. Euclidean distances were calculated with the average linkage method. Data were plotted as either scatter plots of yield percentage vs. BCP percentage or dendrograms showing the different clusters according to the calculated distance.

4. Conclusions The attractiveness of BCP, a natural sesquiterpene present in the essential oil of different plant species, arises from its pharmacological feature as a CB2 receptor agonist. This characteristic, along with the lack of interaction with the CB1, makes BCP an interesting plant endocannabinoid with the advantage of lacking any psychotropic effect, as is typical of some Cannabis extracts [8,311,312]. This systematic analysis of published literature on plant species containing BCP in their essential oils identified the species with the highest yield and BCP content and allowed to select which species are also present in the Belfrit list (i.e., potentially attractive for pharmaceutical and nutraceutical industries). This survey also evidenced the common practice of many authors to ignore the importance of providing the yield of the distilled essential oil, which represent a basic starting point for all industrial applications of the plant species under study. This problem was often correlated with the low amount of plant material distilled. Although interesting from a chemical-analytical point of view, the sole chemical analysis of the essential oil is not useful if performed on a single plant or a few plants, because it does not provide any information on the population genetic variability, being mainly affected by phenotypic plasticity, which is responsible for individual variations inside a population [305]. This work identified some top species like C. langsdforffii, C. odorata, H. lupulus, P. nigrum and S. aromaticum, which provide a high percentage of BCP along with interesting yields. These species, upon a skillful molecular fractionation to remove undesired/toxic monoterpenes, may provide high percentages of BCP that can be used for the preparation of new drugs or dietary supplements aimed to improve health, prevent lifestyle diseases and act as a valid support for chronical diseases such as pain, metabolic and neurological disorders.

Funding: This research was funded by the University of Turin, local research grant number to M.E.M. Conflicts of Interest: The author declares no conflict of interest.

Abbreviations

BCP (E)-β-caryophyllene

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